I have had an iPhone 3G since February 2009. I have not been much of a fan of it, especially over the past summer when the iOS 4.0 update came out. Much of that has been fixed with iOS 4.1.

I am starting to think about getting another phone, and I am hesitant to get an iPhone 4 after the 3G. I am also extremely hesitant to get a smartphone from another maker (WebOS 2.0), but I invested a lot in the past 3-4 years into iTunes with my iPhone and iPod. I have a huge collection in iTunes (40GB+), so I am chained to it.

How can I get a 3rd party smartphone work with iTunes, or atleast be able to pull my collection with a 3rd party software package to sync with my collection or sync with iTunes. I have a Macbook, and use OS X 10.6.4.

If you want to get your music collection onto a non-Apple phone, you can drag and drop the music from the Finder onto the other phone if it supports AAC (I believe Android does, don't know about WebOS) and drag & drop. If the new phone doesn't support AAC, then go into iTunes preferences and change the encoder to mp3, then select all songs in your music library, right-click and select "Create mp3 version". When it's done, go into the Finder and into your iTunes library and drag and drop the mp3s to your device or import them into whatever your using to put music on the new phone.

If you have any protected AAC files from years ago, this won't work for them. You need to make sure upgrade those to DRM-free AAC before you can use this technique. (or you could burn the protected ones to CD then import them back as mp3, but that's kind of convoluted)

As has already been said, you can't sync another manfacturer's phone with iTunes.

AGAIK, iTunes only works with Apple devices. Apple does NOT want iTunes to be able to sync with devices from other mfgrs.

Not quite true.

Early in the iTunes development, it actually supported a variety of 3rd party digital music players. Later on, Apple stopped supporting 3rd party players, and now the only new device support that gets added is for Apple-branded equipment.

As far as I can tell, though, they never took away the existing support for those older 3rd-party devices.

Does the Palm Pre still sync with iTunes or did Apple keep releasing updates until they gave up?

Palm gave up with that tactic when they were informed by the USB-IF (the industry committee that regulates use of the USB standard) that their technique of faking Apple's vendor ID code to trick iTunes into working with WebOS was a breach of Palm's license to use USB technology.

As of today, Palm doesn't offer any Windows or Mac OS X application to sync your WebOS device's music library with your computer. They only directly support over-the-air syncing with online services, and that process normally only applies to contacts, calendars, etc.

Some 3rd party applications have been written, and are advertised on Palm's website, that will act as a go-between to automate a USB tethered sync directly with your computer. Alternatively, when you hook up your WebOS-based device via USB it will appear to be a standard USB hard drive, and you can manually drag-and-drop your compatible music files into the device's music folder.

Palm gave up with that tactic when they were informed by the USB-IF (the industry committee that regulates use of the USB standard) that their technique of faking Apple's vendor ID code to trick iTunes into working with WebOS was a breach of Palm's license to use USB technology.

Just a note: The USB-IF does not license USB technology. Joining them is voluntary. You don't need their permission to make or use USB devices.

What you license from them are voluntary USB ids, and being allowed to use their pretty USB compliance logo.